Presented at the Museum Computer Network conference in Montreal, November 2013. Tweeting, Tumbling, snapping photos--how can we turn typical teen behaviors in the museum into meaningful learning experiences? At the National Gallery of Art, thousands of middle and high school students visit each year. Most are not pre-registered, do not participate in formal educational programs such as tours, and are set loose on their own to explore the museum. To reach and engage this audience, the Gallery created a printed guide to the permanent collection (called #atNGA) that encourages looking carefully at works of art, making connections between art and life, exploring art as historical and cultural expression, and reflecting on the creative spirit. What makes this guide different is that each work of art is paired with a social media prompt such as: take and share a photo (via Instagram), craft a text response (via Twitter), or ponder a question with a friend. By explicitly inviting and helping to shape teens' social media interactions with the Gallery, we hope to turn what might otherwise be a frivolous encounter into a learning experience. This presentation will share the results of our evaluation research and discuss the broader challenges and opportunities of connecting with teens via social media.